The Power of Regret: How Looking Backward Moves Us Forward

While the connection regrets that people reported in the surveys numbered well into the thousands, the specific ways their relationships ended numbered only two: rifts and drifts.

Rifts usually begin with a catalyzing incident—an insult, a disclosure, a betrayal. That incident leads to raised voices, ominous threats, crashed plates, and other mainstays of telenovelas and Edward Albee plays. Rifts leave the parties resentful and antagonistic, even though to outsiders the underlying grievance might sound trivial and easy to repair.

For example, a seventy-one-year-old Canadian man regretted that:

    A disagreement with my son at Christmas over the behavior of his five-year-old son (my grandson) turned into a huge, albeit brief, argument. It has resulted in a family estrangement that has lasted almost five years. We have not talked or communicated in any way since then.



A sixty-six-year-old Texas woman wrote:

    I regret reacting negatively when I found out my daughter-in-law . . . and my son were immigrating back to her home in Australia after we were led to believe she wanted to live near us. They left and are now estranged.



Drifts follow a muddier narrative. They often lack a discernible beginning, middle, or end. They happen almost imperceptibly. One day, the connection exists. Another day, we look up, and it’s gone.

A Pennsylvania woman regretted:

    Not taking time to be a better friend, sister, daughter. Letting time slip away and suddenly realizing that I’m forty-eight.



A forty-one-year-old man in Cambodia wrote:

    I regret letting good friends drift away by not staying in touch.



For many, the situation is recognizable only in retrospect. Said a sixty-two-year-old Pennsylvania man:

    I wish I had tried harder to foster deeper relationships with my work colleagues. I’ve worked at the same place for over thirty years, but I’m not sure I would really call any of the people I’ve worked with a close friend.



Rifts are more dramatic. But drifts are more common.

Drifts can also be harder to mend. Rifts generate emotions like anger and jealousy, which are familiar and easier to identify and comprehend. Drifts involve emotions that are subtler and that can feel less legitimate. And first among these emotions, described by hundreds of people with connection regrets, is awkwardness.

When Cheryl has contemplated reconnecting with her old friend, she’s asked herself, “Would it be better for Jen not ever to hear from me—or for Jen to hear from me and have it be kind of creepy?” And Cheryl’s concerns about creepiness have always prevailed. She worries about “the weirdness of reaching out” after a quarter century. She fears that such a gesture “might seem not right” to her friend.

The same barrier prevented Amy from telephoning Deepa. “There was a sort of awkwardness to me of ‘I haven’t really talked to you in years. But, hey, I heard you’re dying and I’m going to call!’?” Amy explained. “I wish I had not been afraid to confront the uncomfortable feelings I knew I was going to have when I called her.”

If Amy had faced those feelings, she might have been surprised, even gratified. Human beings are impressive creatures. We can fly planes, compose operas, and bake scones. But we generally stink at divining what other people think and anticipating how they will behave. Worse, we don’t realize how inept we are at these skills.[3] And when it comes to perceiving and predicting awkwardness, we’re next-level bunglers.

In a 2014 study, social psychologists Nicholas Epley and Juliana Schroeder recruited commuters on trains and buses in the Chicago area and asked some of them to start conversations with strangers. The recruits predicted that doing so would make them feel uncomfortable and that the recipients of their entreaties would suffer even greater awkwardness. They were mistaken on both fronts. Those who initiated conversations found it easier to do than they expected. They enjoyed their commute more than control group participants, who remained to themselves. And the strangers with whom they spoke were not put off. They enjoyed the conversations just as much.

“People misunderstand the consequences of social connection,” Epley and Schroeder wrote.[4] Commuters feared that reaching out would be uncomfortable for everyone, but their fears were misplaced. It wasn’t awkward at all.

In a 2020 study, Erica Boothby of the University of Pennsylvania and Vanessa Bohns of Cornell University examined a related phenomenon: our squeamishness about complimenting other people. The prospect of giving compliments, Boothby and Bohns found, can make people skittish. They worry “their awkwardness is on display and that people are noticing—and judging—them for their many flaws and faux pas.” But in the experiments, people’s predictions—about themselves and others—proved way off. They drastically overestimated how “bothered, uncomfortable, and annoyed” the person receiving their compliment would feel—and underestimated how positively that person would react.[5] It wasn’t awkward at all.

What’s going on in these situations is a phenomenon that social psychologists call “pluralistic ignorance.” We mistakenly assume that our beliefs differ vastly from everyone else’s—especially when those private thoughts seem at odds with broader public behavior. So, when we struggle to understand a lecture, we don’t ask questions because we erroneously believe that because other people aren’t asking questions, that means they understand—and we don’t want to look dumb. But we don’t consider that other people might be equally befuddled—and equally nervous about seeming stupid. We’re confused, but we stay confused because we falsely believe nobody but us is confused! Or surveys of college students reveal that most students don’t drink excessively. But those students think that they’re the exception, and that all their classmates are constantly getting hammered, which perversely reinforces a social norm that relatively few people truly endorse.[6]

Our concerns about the awkwardness of reconnecting with someone from whom we’ve drifted conform to this pattern. We too often presume that our own preferences are unique. During a conversation in which Cheryl maintained that Jen would have little interest in reconnecting—and that she would instead consider any communication from Cheryl a little creepy—I asked her to consider the reverse scenario.

How would she feel if Jen reached out to her?

“If I got a message from her today, oh my God, I would burst into tears,” she told me. “That would be a life-changing thing for me to hear from her and for her to still be thinking about our friendship after all those years.”





“HAPPINESS IS LOVE. FULL STOP.”

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